Process for the production of tertiary amines and products produced thereby



Patented Mar. 5, 1935 1 TIARY AMINES AND PRODUCTS PRO- DUCED THEREBY Saul Caspe, Brooklyn, N. Y.

No Drawing. Application February 28, 1930, Serial No. 432,264

11 Claims. (01. 260-127l 7 My invention relates to processes for the pro- Among the metallic catalysts suitable for my duction of tertiary amines, their homologues and purpose are copper and platinum and among the derivatives and to new and valuable compounds organic compounds sutable as catalysts are the produced thereby. poly hydroxy alcohols such as glycol, glycerol,

I have found that halogen substituted 'comand mannitol. 5 pounds of the aliphatic series can be converted By "fcatalysts in my specification and claims, into tertiary amino compounds by treating said I mean those compounds which cause the produchalogen compounds with alkyl-amines in the tion of the claimed tertiary amines under atmospresence of catalysts, and that the production of pheric' pressure where such production is not pos- 10 the tertiary amino compounds occurs without the sible in the absence of such catalysts. 10

necessity of increased pressures. What I claim is:-

The present known methods for the production 1. As a new product, diethyl-iso-propylamine of tertiary amines of the character described emof the formula CH3.CHN(C2H5) 2.01-13 and having ploys autoclaves, and similar devices, in order to a boiling point of approximately 108-109 C.

15 obtain increased pressures and hence in addition 2. A process for the production of diethyl-iso- 1 to the expense and difficulty of operation of depropylamine which consists in heating iso-provices of this character, the greatest care must be ply-bromide with N,'N' diethylamine in the presexercised in the application of the required temence of glycerine, perature and pressure, both of which afiect the 3. A process forthe production of diethyl-iso- 0 final results as to yield and quality of produced propylamine which consists in heating iso-propylproducts. bromide with N, N diethylamine in the presence I have overcome the above mentioned, and of glycerine under arefiux condenser. other, objectionable features of the present em- 4. A process for the production of tertiary ployed processes in that I employ a reflux conamines which consists in heating an alkyl halide denser, thus obtaining an approximately uniform of the aliphatic series having not more than 5 25 temperature throughout the reaction and obtaincarbon atoms with a dialkyl amine having not ing practically theoretical yields of the produced more than 5 carbon atoms in the presence of glycompounds. cerine.

I give the following as one method of the proc- 5. A process for the production of tertiary ess of my invention:-- amines which consists in heating an alkyl mono-. 30

1 mol isopropyl bromide, 1 mol diethylamine halide of the aliphatic series having not more and .5 mol glycerine are heated together in a than 5 carbon atoms with a dialkyl amine having reflux condenser for several days. The mixture not more than 5 carbon atoms in the presence or is made alkaline with sodium hydrate and exglycerine.

tracted several times with ether. The ether solu- 6. A process for the production of tertiary 35 tion is dried with potassium hydrate sticks, filamines which consists in heating an alkyl monotered, evaporated and the diethyl-iso-propylbromide of the aliphatic series having not more amine thus formed is distilled. The diethyl-isothan 5 carbon atoms with a dialkyl amine having propylamine thus formed has the formula not more than 5 carbon atoms in the presence of glycerine under a reflux condenser. 40

CH3'CHN(C2H5)2'CH3 I 7. A process for the production of tertiary with a boiling point of l08-109 C. amines which consists in heating an alkyl halide I do not limit myself to the isopropyl bromide of the aliphatic series having not more than 5 carmentioned in the above example, as other similar bon atoms with a dialkyl'amine having not more halogen compounds can be employed such as the than 5 carbon atoms in the presence of a poly- 45 halogenated compounds of the isomeric propyl hydroxy alcohol catalyst. compounds, butyl compounds and the other hom- 8. A process for the production of tertiary ologues of this chemical series, and halogen comamines which consists in heating an alkyl monopounds other than the bromide may be employed halide of the aliphatic series having not more among which are the chlorides and iodides. than 5 carbon atoms with a dialkyl amine having 50 Neither do I limit myself to the particular dinot more than 5 carbon atoms in the presence of a ethylamine mentioned in the above example, as poly-hydroxy alcohol catalyst. other alkyl amines may be employed, among 9. A process for the production of tertiary which are ethylamine and dimethylamine, amines which consists in heating an alkyl halide methylamine and similar amines. of the aliphatic series having not more than 5 55 carbon atoms with a di-alkyl amine having not more than 5 carbon atoms in the presence of glycerine.

10. A process for the production of tertiary amines which consists in heating an alkyl monohalide of the aliphatic series having not more than 5 carbon atoms with a di-alkyl amine having not more than 5 carbon atoms in the presence of glycerine.

SAUL CASPE. 

